Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_142488,IEDB_146664,IEDB_2116141,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

• Article ID: 3465
  Fedonenko YP, Zdorovenko EL, Konnova SA, Kachala VV, Ignatov VV "Structural analysis of the O-antigen of the lipopolysaccharide from Azospirillum lipoferum SR65" - Carbohydrate Research 343(16) (2008) 2841-2844
  

  A neutral O-polysaccharide was obtained by mild acid degradation of the lipopolysaccharide isolated by phenol/water extraction from the asymbiotic diazotrophic rhizobacterium Azospirillum lipoferum SR65. The following structure of the O-polysaccharide was established by composition and methylation analyses, Smith degradation, and 1H and 13C NMR spectroscopy, including a 2D ROESY experiment:

  Lipopolysaccharide, bacterial polysaccharide structure, Azospirillum lipoferum

  NCBI PubMed ID: 18561903
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: E.L. Zdorovenko
  Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, Prospekt Entuziastov 13, 410049 Saratov, Russia.
  Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, chemical analysis, Smith degradation
  
   
  
  Azospirillum brasilense S17
  CSDB ID 22939 (all data & tools)
• Article ID: 3466
  Fedonenko YP, Konnova ON, Zatonsky GV, Konnova SA, Shashkov AS, Zdorovenko EL, Ignatov VV, Knirel YA "Structural studies of the polysaccharides from the Azospirillum brasilense S17 lipopolysaccharide" - Carbohydrate Research 343(4) (2008) 810-816
  

  A mixture of two structurally distinct neutral O-polysaccharides was obtained by mild acid degradation of the lipopolysaccharideisolated by the phenol/water extraction from the asymbiotic diazotrophic rhizobacterium Azospirillum brasilense S17.The following structures of the O-polysaccharides were established by composition and methylation analyses, Smith degradation,and 1H and 13C NMR spectroscopy, including a 2D NOESY experiment: where L-Rha2Me stands for 2-O-methyl-L-rhamnose and SHb for the (S)-3-hydroxybutanoyl group. The occurrence of two distinct polysaccharides is reported for the first time in Azospirillum spp.2007 Elsevier Ltd. All rights reserved

  Lipopolysaccharide, Azospirillum brasilense, bacterial polysaccharide structure, 2-O-Methyl-L-rhamnose

  NCBI PubMed ID: 18226805
  Publication DOI: 10.1016/j.carres.2007.12.013
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: E.L. Zdorovenko
  Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, Prospekt Entuziastov 13, 410049 Saratov, Russia, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, Smith degradation, composition analysis
  
   
  
  Azospirillum brasilense S17
  CSDB ID 22941 (all data & tools)
• Article ID: 4016
  Fedonenko YP, Boyko AS, Zdorovenko EL, Konnova SA, Shashkov AS, Ignatov VV, Knirel YA "Structural pecularities of the O-specific polysaccharides of Azospirillum bacteria of serogroup III" - Biochemistry (Moscow) 76(7) (2011) 797-802
  

  Azospirillum brasilense SR55, isolated from the rhizosphere of Triticum durum, was classified as serogroup II on the basis of serological tests. Such serogroup affiliation is uncharacteristic of wheat-associated Azospirillum species. The lipid A of A. brasilense SR55 lipopolysaccharide contained 3-hydroxytetradecanoic, 3-hydroxyhexadecanoic, hexadecanoic and octadecenoic fatty acids. The structure of the lipopolysaccharide's O polysaccharide was established, with the branched octasaccharide repeating unit being represented by l-rhamnose, l-3-O-Me-rhamnose, d-galactose and d-glucuronic acid. The SR55 lipopolysaccharide induced deformations of wheat root hairs. The lipopolysaccharide was not involved in bacterial cell aggregation, but its use to pretreat wheat roots was conducive to cell adsorption. This study shows that Azospirillum bacteria can utilise their own lipopolysaccharide as a carbon source, which may give them an advantage in competitive natural environments.

  Lipopolysaccharide, O-antigen, O-Polysaccharide structure, serological characterization, Azospirillum

  NCBI PubMed ID: 21999541
  Publication DOI: 10.1134/S0006297911070108
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Correspondence: room308@ibppm.sgu.ru
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Laboratory of Biochemistry, Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 13 Prospekt Entuziastov, Saratov 410049, Russia, Saratov State University, ul. Astrakhanskaya 83, 410012 Saratov, Russia
  Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, SDS-PAGE, sugar analysis, acid hydrolysis, GLC
  
   
  
  Azospirillum brasilense S17
  CSDB ID 26617 (all data & tools)
• Article ID: 4329
  Knirel YA "Structure of O-antigens" - Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
  

  The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.

  Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis

  Publication DOI: 10.1007/978-3-7091-0733-1_3
  Publisher: Springer
  Correspondence: knirel@ioc.ac.ru
  Editors: Knirel YA, Valvano MA
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Azospirillum brasilense S17
  CSDB ID 27854 (all data & tools)
• Article ID: 4824
  Sigida EN, Fedonenko YP, Shashkov AS, Zdorovenko EL, Konnova SA, Ignatov VV, Knirel YA "Structure of the polysaccharides from the lipopolysaccharide of Azospirillum brasilense Jm125A2" - Carbohydrate Research 416 (2015) 37-40
  

  Two polysaccharides were obtained by mild acid degradation of the lipopolysaccharide of associative nitrogen-fixing bacteria Azospirillum brasilense Jm125A2 isolated from the rhizosphere of a pearl millet. The following structures of the polysaccharides were established by sugar and methylation analyses, Smith degradation, and (1)H and (13)C NMR spectroscopy: [Formula: see text] Structure 1 has been reported earlier for a polysaccharide from A.?brasilense S17 (Fedonenko YP, Konnova ON, Zdorovenko EL, Konnova SA, Zatonsky GV, Shaskov AS, Ignatov VV, Knirel YA. Carbohydr Res 2008;343:810-6), whereas to our knowledge structure 2 has not been hitherto found in bacterial polysaccharides.

  Lipopolysaccharide, Azospirillum brasilense, bacterial polysaccharide structure

  NCBI PubMed ID: 26343325
  Publication DOI: 10.1016/j.carres.2015.08.011
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: si_elena@mail.ru (E.N. Sigida)
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, Prospekt Entuziastov 13, 410049 Saratov, Russia, Chernyshevsky Saratov State University, Ulitsa Astrakhanskaya 83, 410012 Saratov, Russia
  Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, GLC, mild acid hydrolysis, Smith degradation, composition analysis, GPC
  
   
  
  Azospirillum brasilense Jm125A2, Azospirillum brasilense S17
  CSDB ID 30728 (all data & tools)
• Article ID: 4844
  Fedonenko YP, Sigida EN, Konnova SA, Ignatov VV "Structure and serology of O-antigens of nitrogen-fixing rhizobacteria of the genus Azospirillum" - Russian Chemical Bulletin = Izvestiia Akademii nauk. Seriia khimicheskaia 64(5) (2015) 1024-1031
  

  The review presents a discussion of the published data of 2002 to 2014 dealing with structural studies of O-specific polysaccharides, representatives of the Azospirillum diazotrophic rhizobacteria, summarizing the results of a series of authors? studies. Some general structures incorporated in O-specific polysaccharides responsible for classification of bacterial cultures into serogroups on the basis of immunochemical studies were characterized. The structures of O-specific polysaccharides of seven azospirillum strains identical to those of previously studied strains are presented in this review for the first time.

  lipopolysaccharides, O-specific polysaccharides, Structures, Azospirillum, O-antigenic determinants

  Publication DOI: 10.1007/s11172-015-0971-x
  Journal NLM ID: 100912060
  Publisher: New York: Consultants Bureau
  Correspondence: si_elena@mail.ru
  Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms Russian Academy of Sciences, 13 prosp. Entuziastov, 410049 Saratov, Russian Federation
  
   
  
  Azospirillum brasilense S17, Azospirillum brasilense SR7
  CSDB ID 11169 (all data & tools)
• Article ID: 4974
  Abronina PI, Burygin GL, Kononov LO "Synthesis of fragments of O-antigenic polysaccharides of nitrogen-fixing rhyzobacteria of the genus Azospirillum" - Russian Chemical Bulletin = Izvestiia Akademii nauk. Seriia khimicheskaia 65(6) (2016) 1448-1463
  

  Fragments of Oantigen polysaccharides of nitrogenfixing rhizobacteria of the genus Azospirillum isolated from natural sources may greatly vary in the monosaccharide composition, molecular weight, as well as in the presence of side chains and branching sites along the main chain. These variations, along with the differences in purity and homogeneity of the samples, hamper investigations of the role of individual components of Oantigen polysaccha rides of the rhizobacteria Azospirillum in interactions with plants, including important cereal crops. Therefore, synthetic oligosaccharides, which correspond to Oantigen polysaccharide fragments of rhizobacteria of the genus Azospirillum and have a strictly defined structure and high purity, are highly demanded. The review summarizes the data on the synthesis of these oligosaccharide fragments as promising tools for investigation of the mechanism of formation of a symbiotic association with plants.

  synthesis, O-antigens, polysaccharides, fragment, nitrogen fixing, 1, Azospirillum, 2-cisglycosylation

  Publication DOI: 10.1007/s11172-016-1472-2
  Journal NLM ID: 100912060
  Publisher: New York: Consultants Bureau
  Correspondence: polinaabronina@yandex.ru; kononov@ioc.ac.ru
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., Moscow, Russian Federation, Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 13 prosp. Entuziastov, 410049 Saratov, Russian Federation
  Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, chemical methods, MS, glycosylation
  
   
  
  Azospirillum brasilense S17(1) (II)
  CSDB ID 11854 (all data & tools)
• Article ID: 5498
  Sigida EN, Fedonenko YP, Shashkov AS, Toukach PV, Shelud'ko AV, Zdorovenko EL, Knirel YA, Konnova SA "Structural studies of O-specific polysaccharide(s) and biological activity toward plants of the lipopolysaccharide from Azospirillum brasilense SR8" - International Journal of Biological Macromolecules 126 (2019) 246-253
  

  Lipopolysaccharide (LPS) was extracted from dry bacterial cells of plant-growth-promoting bacterium Azospirillum brasilense SR8 (IBPPM 5). The O-specific polysaccharide (OPS) was obtained by mild acid hydrolysis of the lipopolysaccharide and studied by sugar analysis, 1H and 13C NMR spectroscopy, including 1H,1H COSY, TOCSY, ROESY, and 1H,13C HSQC and HMBC experiments, computational NMR-based structure analysis, and Smith degradation. The OPS was shown to contain two types of repeating units of the following structure: Both OPS structures are present in A. brasilense 54, from which structure 1 has been reported earlier (Fedonenko et al., 2011), whereas to our knowledge structure 2 has not been hitherto found in bacterial saccharides. Treatment of wheat seedling roots with LPS of A. brasilense SR8 increased the number of root hair deformations as compared to seedlings grown without LPS, but had no effect on adsorption of the bacteria to the root surface. A. brasilense SR8 was able to utilize LPS of several structurally related Azospirillum strains.

  Lipopolysaccharide, structure, O-specific polysaccharide, Azospirillum brasilense, Chemotaxis, NMR simulation, Root hair deformation

  NCBI PubMed ID: 30590146
  Publication DOI: 10.1016/j.ijbiomac.2018.12.229
  Journal NLM ID: 7909578
  Publisher: Butterworth-Heinemann
  Correspondence: E.N. Sigida
  Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 13 Prospect Entuziastov, Saratov 410049, Russia, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, Moscow, Russia, N. G. Chernyshevsky Saratov State University, 83 Ulitsa Astrakhanskaya, Saratov 410012, Russia
  Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, de-O-acylation, SDS-PAGE, sugar analysis, acid hydrolysis, GLC, GC, Smith degradation, GPC, 13C NMR analysis by GRASS, experiments on plants
  
   
  
  Azospirillum brasilense S17, Azospirillum brasilense SR7, Azospirillum brasilense Jm125A2
  CSDB ID 2296 (all data & tools)
• Article ID: 5846
  Sigida EN, Kokoulin MS, Dmitrenok PS, Grinev VS, Fedonenko YP, Konnova SA "The Structure of the O-Specific Polysaccharide and Lipid A of the Type Strain Azospirillum rugosum DSM-19657" - Russian Journal of Bioorganic Chemistry 46(1) (2020) 60-70
  

  The paper reports the structural study of the lipopolysaccharide from the type strain of the soil nitrogen-fixing bacterium Azospirillum rugosum isolated from oil-polluted soils. Based on the chemical analysis and 1D- and 2D 1H and 13C NMR spectroscopy data it has been demonstrated that the O-specific polysaccharide consists of the two types of repeating units identical to those previously described for the O-specific polysaccharide of the Azospirillum brasilense strain Jm125A2. Structural analysis of the lipid A using gas-liquid chromatography (GLC) and MALDI mass spectrometry revealed the presence of penta-, tetra-, and triacylated species. The primary fatty acids in the lipid A are the N-linked 16:0(3-OH) and O-linked 14:0(3-OH). Microheterogeneity within each species arises from the presence of different secondary fatty acids (16:0, 18:1, or 19:0) acylating the 16:0(3-OH) acid of the distal GlcN ring.

  Lipopolysaccharide, lipid A, NMR spectroscopy, O-specific polysaccharide, Azospirillum rugosum, MALDI mass spectrometry

  Publication DOI: 10.1134/S1068162020010112
  Journal NLM ID: 9420101
  Publisher: Springer Science and Business Media
  Correspondence: si_elena@mail.ru
  Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 410049, Saratov, Russia, Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch, Russian Academy of Sciences, 690022, Vladivostok, Russia, Chernyshevskii Saratov National Research State University, 410012, Saratov, Saratov oblast, Russia
  Methods: 13C NMR, 1H NMR, methylation, gel filtration, NMR-2D, de-O-acylation, sugar analysis, acid hydrolysis, GLC, GC, MS/MS, MALDI-TOF MS, composition analysis
  
   
  
  Azospirillum rugosum DSM-19657, Azospirillum brasilense Jm125A2
  CSDB ID 7569 (all data & tools)